Best Manager Ever

In this special holiday spoof episode of Best Manager Ever,  Annie Riley, host and founder of Fort Light, chats with the one and only Santa Claus!Known for spreading holiday cheer and managing a diverse team at the North Pole, Santa gives a rare interview about life behind the scenes. His direct reports, including elves and reindeer, praise Santa for his leadership, though they note he's their only manager ever ;) We will dive into Santa's leadership style, the secrets behind the naughty and nice lists, and the challenges of maintaining the Christmas spirit all year long. Join us for a fun-filled episode with laughter and insight into the man behind the magic.Connect with Annie RileyConnect with our hilarious Santa, Jason GoreListen to Jason’s podcast 108.9 The HawkCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

In this recap episode of Best Manager Ever, host Annie Riley reflects on standout lessons from Season 3.Annie discusses the six things our top manager guests have in common: high standards, clear communication, strong relationships with peers, a relentless focus on their own growth, a unique view of career management, and a human-first perspective. It’s a chance to pause, look back, and notice what makes our guests so exceptional— and then think about how to apply those lessons in your own work. Whether you're a longtime listener or just tuning in, this episode offers a meaningful recap of the themes that shaped our season. Share your feedback and suggestions from the season in this super quick form, so we can make future episodes even better. If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Jared Erondu is a seasoned design and startup leader, and is currently the Head of Design at early-stage startup Span. Jared spent eight years at Lattice rising from a solo designer pulling all-nighters in the early days, to leading a 50-person design organization and serving as GM across product and GTM as the company scaled. Earlier in his career, he was a design leader at Teespring and Omada Health. Jared is known for his design mentorship and community-building, and is an active advisor and angel investor. Jared brings a calm, steady presence, especially during challenging times, always seeing the long view and providing unwavering support. His team appreciates his high standards, attention to detail, and commitment to craft, but also noted that he balances intensity with humor and approachability.In this episode, show creator and Fort Light founder Annie Riley sits down with Jared, and they discuss:Why all managers should master selective transparencyThe right way to communicate destabilizing intel How to recondition your mindset for “hard mode” leadershipHow to build a bench of resources to support yourself  The best way to recruit exceptional talent Why managing your own mindset is the ultimate leadership unlock If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.comJoin us on Substack Connect with Jared EronduConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Dana Lawson is the CTO of Netlify. She’s been a technologist for decades, and was previously the VP of Engineering at Github and the Director of Engineering at New Relic, Heptio, InVision (acquired by Miro), and more. Dana has a diverse background, and served in the military. Dana's direct reports praise her for building confidence, providing autonomy support, for bringing honesty and compassion, and for sponsorship that goes beyond mentorship. In this episode, show creator and Fort Light founder Annie Riley sits down with Dana, and they discuss:How imposter shows up at senior levels– and how to handle it  How to deal with interpersonal conflictsWhat it takes to be an effective sponsorThe importance of embracing changeIf you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.comJoin us on Substack Connect with Dana LawsonConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Amit Shah is the COO of Virta Health, where he’s built the company from ~30 team members to over 800 colleagues working to reverse obesity and diabetes. Amit has 10+ years of experience in building and scaling entrepreneurial and high-growth healthcare organizations, with a focus on delivering financial and operational results while aligning on mission and values.Amit’s direct reports praise his ability to balance the needs of Virta’s members, business, and staff, describing him as incredibly kind, caring, driven, and a fierce protector of his team. He is celebrated for his passion, structured thinking, dedication to his own growth and development, and continuous improvement in leadership.In this episode, show creator and Fort Light founder Annie Riley sits down with Amit,and they cover:How to build a gratitude practice that supports your team – and yourselfThe importance of emotional awareness and regulation in leadership Energy management habits and practices   A process to take charge of feedback, learning, and growth The relationship between execution and strategy in startups If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Amit Shah Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Patrick Reynolds is the Co-Founder and Head of Product at Office Hours, an expert marketplace. Patrick started his career as a software engineer, before becoming a self-taught product designer and making the leap into product leadership. He has worked at an array of tech companies and startups including Affirm, Sweep, and Adobe. Patrick's direct reports praise him for his exceptional thoughtfulness, noting his ability to remember personal details and small, meaningful actions that remove friction and boost morale. They describe him as a natural coach who not only sets high standards but also provides the necessary support and resources to achieve them. In this episode, show creator and Fort Light founder Annie Riley sits down with Patrick, and they discuss:The difference between leadership and management  How to prime yourself so it’s easy to spot opportunities to support your team The difference between a culture that inspires ambition vs. enforces it How to consume content for maximum ROI The best way to spot (and stop!) perfectionism If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Patrick ReynoldsConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Sophie Ruddock brings deep expertise in scaling mission-driven tech companies, and is now the COO at Empathy. Sophie was an early employee at Multiverse, where she grew with the company and ultimately became their global COO leading through rapid growth and market expansion. Sophie’s direct reports praise her empowering leadership style, her commitment to their development, and her unwavering advocacy. She hires people for their unique expertise and encourages them to bring their full selves to work, and reminds them of their value even in moments of self-doubt.In this episode, show creator and Fort Light founder Annie Riley sits down with Sophie, and they discuss:What a “founder mindset” really means for employees How to earn the right to dissent How to lead when someone on the team has an unexpected crisis The mindset shift that enabled Sophie to go from managing 3 to 600+ people If you’re interested in sponsoring an episode of Best Manager Ever, reach out:  sponsor@fortlight.comJoin us on Substack Connect with Sophie RuddockConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

In this expert episode, Annie Riley sits down with Matt Wallaert, an applied behavioral scientist who made the leap into the tech and startup worlds. Matt is currently the CXO at Oceans, and he’s previously held leadership roles at Clover Health, LendingTree, Microsoft, frog design, and more. Matt explains why all leaders should know and use the principles of applied behavioral science– because all startup leaders are in the business of behavior change with our customers, our teams, and ourselves. They discuss specific tactics that leaders can use to influence their team’s behavior, including the SIDE framework, promoting and inhibiting pressures, iterative experimentation, and more. Matt explains how applied behavioral science can be the key to unlocking lasting and meaningful behavior change, and to achieving a more empathetic and effective leadership style. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Matt WallaertConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

​​In this special Halloween episode of Best Manager Ever, host Annie Riley recounts the top worst manager moments of her career. Tune in to hear scary manager stories, from tales of micromanagement to vague (and unsettling!) feedback… and even Annie’s own manager missteps. There’s value in learning from the best, and ALSO from the worst! You’ll finish this episode feeling less alone, and even with some actionable lessons to help you avoid the same manager mistakes. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Amy Yamner Jenkins is the Chief Operating Officer at Meadow, which is an early-stage fintech startup working to transform the financial experience for students and universities. Amy started her career as a classroom teacher, and pivoted into startups by working at NewSchools Venture Fund. Before Meadow, she had a long and successful chapter building Education Elements, and then led the partnerships team at Outschool. Amy’s direct reports describe her as an empowering leader, someone who provides useful and constructive feedback, fosters a high-trust environment, and enables team members to grow.In this episode, show creator and Fort Light founder Annie Riley sits down with Amy,and they discuss:Why connection and context should come before content How to notice and combat bias in hiring A simple 2x2 framework to exchange feedback with your team Why you should avoid using common words like “obviously” and “of course” as a leader If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Amy JenkinsConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Adam Fishman is a product and growth advisor with 20+ years of experience building and leading startup teams. Adam was on the early team at Lyft, where he served as Head of Growth. He then went on to lead Product & Growth at Patreon and Imperfect Foods, before launching his portfolio career. Adam has been an advisor and fractional leader at ResortPass, Mozilla, HelpScout, Peerspace and more. He is also the creator of FishmanAF newsletter and the host of the Startup Dad podcast. Adam’s direct reports praise him for his exceptional support, trust, and empowerment, as is recognized as a catalyst who brings people together across teams, fostering high trust and commitment. His team members appreciate his transparency, proactive communication, and the way he sets clear mutual expectations. In this episode, show creator and Fort Light founder Annie Riley sits down with Adam, and they discuss:How to build trust quickly as a new leader or fractional executive, and why starting from a place of trust matters.How to get more honest feedback from your direct reportsThe best way to manage defensiveness when receiving feedback– and how Adam learned it the hard way Predictions for how AI will impact product leadership roles Why distributing credit and advocating for your team’s growth leads to higher performance and engagement.If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Adam FishmanConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Lauren Gold is the Chief Customer Officer at Kustomer, an AI-powered CX platform. Lauren began her tech career at Yahoo before joining the early team at Yext, where she rose from individual contributor to SVP of Enterprise Customer Success. Lauren’s direct reports and colleagues describe her as a leader who supports without micromanaging, fosters autonomy, and creates an environment where everyone feels comfortable sharing, learning, and growing. She’s recognized for her attention to detail, data-driven approach, and willingness to jump in and help, while always encouraging her team to take ownership and develop their own skills.In this episode, show creator and Fort Light founder Annie Riley sits down with Lauren to discuss:How to start well in new roles and build trust quicklyThe art of supporting teams without micromanagingTransitioning from first-line leader to managing managersSpotting and developing leadership talent within your teamThe importance of over-communication and transparency in leadershipWhy building relationships and understanding individual motivations matterIf you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Lauren GoldConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Charlie Coglianese is the Chief Technology Officer at Paloma Learning, a VC-backed edtech startup using AI to improve student learning outcomes. Charlie started his career in finance, before making the leap into startups. He was the Founder & CEO of a startup called Schoolrunner, which was acquired by SchoolMint. Charlie served as the CTO at SchoolMint post-acquisition before returning to early-stage building in his current roleCharlie's direct reports describe him as a leader who invests deeply in the growth of his team. He’s recognized for his ability to spot potential, provide the right level of challenge, and create an environment where people feel trusted to take ownership, try new things, and grow. The most common theme in their feedback is that Charlie empowers his team—he’s known for his intellectual honesty, willingness to jump in alongside his team, and his focus on building trust and clarity.In this episode, show creator and Fort Light founder Annie Riley sits down with Charlie, and they discuss:How to spot talent through trajectory, instead of outcomesThe concept of “productive struggle” and how to balance challenge and supportAdvice for working with founders and navigating the founder-executive relationshipStrategies for retaining top performers and keeping them engagedThe importance of clear goals and mission in motivating teamsIf you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Charlie CoglianeseConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Karin Simelaro is the Chief Revenue Officer at SchoolAI, an AI platform that supports teacher and student success. Previously, Karin served as the Revenue leader at BrainPOP, Pathful, and Seesaw. She was an early employee at Nearpod, where started as the first field sales rep when the company was fewer than 30 people and around $10M ARR, and ultimately grew the business to $100M ARR and a successful exit. Karin’s direct reports describe her as open, transparent, energetic, and having high expectations for herself and her team. Her unique blend of skills positions her as a key player in the intersection of education and technology, poised to shape the future of learning.In this episode, show creator and Fort Light founder Annie Riley sits down with Karin,and they discuss:How to evaluate performance amid the uncertainty of early-stage building using the “REKS” framework The importance of a weekly “coffee and contemplation” How to act like an owner of the business – whether you’re an IC or C-level Using AI to prepare and clarify your thoughtsIf you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Karin SimelaroConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Darius Contractor is the Chief Growth Officer at Otter AI. Darius has had a long and impactful career in the startup and tech worlds. Prior to Otter AI, he led engineering, growth and product teams at Vendr, Airtable, Facebook, Dropbox, Bebo and more. He is also an investor and advisor in multiple companies and funds. Darius’s direct reports describe him as a master of frameworks and analogies, someone who balances detail orientation with a big-picture vision, and a manager who pushes boundaries with unconventional but memorable approaches.In this episode, show creator and Fort Light founder Annie Riley sits down with Darius,and they discuss:How to support your team’s career path in a fast-paced, high-growth environment The SEEN framework for career development Designing jobs like dinner plates How frameworks and analogies make concepts more memorable If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Darius ContratorConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Stevie Case is the Chief Revenue Officer at Vanta. Stevie started her career as the world’s first female pro gamer, and then found her way into the tech and startup world through a self-described “winding path”. Prior to Vanta, Stevie had a successful chapter at Twilio, where she started as an individual contributor and then grew to be the VP of Mid-Market Sales.Stevie’s direct reports consistently describe her as an empowering leader who excels at identifying and nurturing the unique strengths of each individual on her team. They highlight her ability to create an environment where people feel trusted to be themselves, try new things, and take ownership of their work. The most common theme in their feedback is that Stevie makes her team members feel empowered—she is known as a “yes, and…” leader who encourages innovation and supports her team’s ideas, while also setting a high bar for performance and a strong drive to win.In this episode, show creator and Fort Light founder Annie Riley sits down with Stevie, and they discuss:How Stevie has moved between IC and manager roles in her career (and why!) What a manager’s real job is— according to Stevie Why your direct reports are not your “first team” How Stevie vetted Christina as a potential CEO and boss How Stevie’s communication style has evolved as she’s become more senior and Vanta has scaled Why you should prioritize sharing your own story on LinkedIn, even amid a busy startup schedule If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Stevie CaseConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Best Manager Ever shares unfiltered leadership lessons and actionable advice from the most successful and beloved leaders in the startup and tech worlds. This season, you'll hear honest, insightful interviews with operators who’ve been nominated by their teams as the best manager they’ve ever worked for. And for the first time, we’re adding interviews with experts who’ve gone deep on the leadership topics that matter most to you.Each episode is designed to share actionable advice that helps you level up as a leader— almost like a seasoned mentor in your pocket and in your corner. All you have to do is show up and hit play, and we’ll give you something valuable that you can apply in your own work and life. Season 3 starts September 10th and new episodes drop every Wednesday. Subscribe to make sure you never miss an episode, and join the conversation on Substack. If you’re interested in sponsoring an episode of Best Manager Ever, reach out: sponsor@fortlight.comJoin us on Substack Connect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s Producer, Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Sruthi Lanka serves as CFO of Public, an investing platform that allows everyone to invest in stocks, ETFs, crypto, and alternative assets, like fine art and collectibles—all in one place. Prior to Public, she was VP Finance at MoneyLion, a consumer lending platform that listed on NYSE via SPAC in 2021. Her previous career was in investment banking at the Royal Bank of Canada and technology at Goldman Sachs.Sruthi's direct reports praise her coaching and context-driven leadership approach, maintaining lean teams while investing heavily in tools and automation, fostering a metrics-driven mindset, and the importance of authenticity and personal connection in leadership.In this episode, show creator and Fort Light founder Annie Riley sits down with Sruthi, and they cover:Recruiting 'scary' talent to push the company's boundariesHow to build cross-functional expertiseMaintaining a strong understanding of company metricsPromoting a culture where lean teams are empowered How to integrate joy into workJoin us on Substack Connect with Sruthi LankaConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Asheesh Birla is an Entrepreneur, Angel Investor and Ripple Board Member. Asheesh joined Ripple in 2013 when the team was fewer than ten people. He had a decade-long journey of building Ripple on the product team, and he continues to stay connected to the company as a member of the board. Asheesh’s  direct reports admire his passion, strategic vision, and ability to cultivate a positive work culture. They praise his direct communication, commitment to personal development, and knack for making tough situations enjoyableIn this episode, show creator and Fort Light founder Annie Riley sits down with Asheesh, and they cover:How to set high standards and expectations while maintaining trust and motivationThe importance of coaching – for yourself and your teamEffective strategies to develop and retain talentThe importance of communicating in a direct and caring wayMethods to handle difficult situations with positivityJoin us on Substack Connect with Asheesh BirlaConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.

Lauren Rhode is the VP of Sales at Webflow, and she’s had several interesting chapters to her career. Lauren got her start in public service, working at the Department of Defense. She also played on the national rugby team, and traveled around the world competing for Team USA. She started her tech career in product, before discovering her knack for sales. She has held prior roles at Bablestreet (formerly Vertical Knowledge) and Anaplan.Lauren's direct reports describe her as a hardworking and empathetic leader. She is known as a “machine”, while also fostering a positive team culture where everyone feels valued and supported.In this episode, show creator and Fort Light founder Annie Riley sits down with Lauren, and they cover:Dealing with leadership transitions in scaling companies How to show up deliberately in virtual interactionsEmpowering teams with optimistic realismManaging your time and schedule intentionally as a leaderJoin us on Substack Connect with Lauren RhodeConnect with Annie RileyCheck out Fort Light to level up your leadership skillsConnect with our show’s producer Alexis RamdaouNominate your Best Manager Ever for the PodcastThis is a Production of Fort Light and Now it’s Hear Hosted on Acast. See acast.com/privacy for more information.